So the ultimate question is...
Did Connor McDavid wake up on contract day and say, "I'm the best player on the planet but I purposely want to be criminally underpaid for my production so I'll sign 8 years..."
Or...
Does he say, "I can demand the Oilers pay me every penny I ask for but I won't because I want to be part of a competitive team for 8 years..."?
I think we know the answer. The difference between a person like McDavid and a person like Matthews is their drive, perspective, priorities, dedication, and ultimate thirst to become a champion.
MacKinnon did the same thing McDavid did and got his Cup. If Matthews cared as much about getting his name on the Cup as he does maximizing every penny he's paid by the Leafs, he'd be on his way to becoming a modern day Henri Richard.